Actaplanin

Last updated
Actaplanin
Actaplanin 1.png
Names
Other names
Antibiotic A 4696, Kamoran
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C90H101ClN8O40/c1-29-47-18-35(19-48(29)132-88-75(116)71(112)67(108)54(26-101)135-88)61-83(122)97-62-36-20-51(129-38-9-4-31(5-10-38)14-43(80(119)95-61)94-81(120)59(93)32-6-12-45(105)49(17-32)131-47)79(139-90-77(118)73(114)69(110)56(137-90)28-127-87-74(115)70(111)66(107)53(25-100)134-87)52(21-36)130-46-13-8-34(16-41(46)91)78(138-57-24-42(92)65(106)30(2)128-57)64-85(124)98-63(86(125)126-3)40-22-37(103)23-50(133-89-76(117)72(113)68(109)55(27-102)136-89)58(40)39-15-33(7-11-44(39)104)60(82(121)99-64)96-84(62)123/h4-13,15-23,30,42-43,53-57,59-78,87-90,100-118H,14,24-28,92-93H2,1-3H3,(H,94,120)(H,95,119)(H,96,123)(H,97,122)(H,98,124)(H,99,121)
    Key: PFEBYWJUETVBLJ-UHFFFAOYSA-N
  • CC1C(C(CC(O1)OC2C3C(=O)NC(C4=C(C(=CC(=C4)O)OC5C(C(C(C(O5)CO)O)O)O)C6=C(C=CC(=C6)C(C(=O)N3)NC(=O)C7C8=CC(=C(C(=C8)OC9=C(C=C2C=C9)Cl)OC1C(C(C(C(O1)COC1C(C(C(C(O1)CO)O)O)O)O)O)O)OC1=CC=C(CC2C(=O)NC(C3=CC(=C(C(=C3)OC3C(C(C(C(O3)CO)O)O)O)C)OC3=C(C=CC(=C3)C(C(=O)N2)N)O)C(=O)N7)C=C1)O)C(=O)OC)N)O
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Actaplanin is a complex of broad-spectrum antibiotics made by Actinoplanes bacteria. [1] [2] Research carried out by a group in Eli Lilly and Co. in 1984 identified several actaplanins using high-performance liquid chromatography. [3] [4] [5] Actaplanins A, B1, B2, B3, C1 and G were shown to be composed of the same peptide core, an amino sugar, and varying amounts of glucose, mannose, and rhamnose. [6]

See also

Related Research Articles

<span class="mw-page-title-main">Riboflavin</span> Vitamin, dietary supplement, and yellow food dye

Riboflavin, also known as vitamin B2, is a vitamin found in food and sold as a dietary supplement. It is essential to the formation of two major coenzymes, flavin mononucleotide and flavin adenine dinucleotide. These coenzymes are involved in energy metabolism, cellular respiration, and antibody production, as well as normal growth and development. The coenzymes are also required for the metabolism of niacin, vitamin B6, and folate. Riboflavin is prescribed to treat corneal thinning, and taken orally, may reduce the incidence of migraine headaches in adults.

Vitamin B<sub>6</sub> Class of chemically related vitamins

Vitamin B6 is one of the B vitamins, and is an essential nutrient for humans. The term essential nutrient refers to a group of six chemically similar compounds, i.e., "vitamers", which can be interconverted in biological systems. Its active form, pyridoxal 5′-phosphate, serves as a coenzyme in more than 140 enzyme reactions in amino acid, glucose, and lipid metabolism.

<span class="mw-page-title-main">Vancomycin</span> Antibiotic medication

Vancomycin is a glycopeptide antibiotic medication used to treat certain bacterial infections. It is administered intravenously to treat complicated skin infections, bloodstream infections, endocarditis, bone and joint infections, and meningitis caused by methicillin-resistant Staphylococcus aureus. Blood levels may be measured to determine the correct dose. Vancomycin is also taken orally to treat Clostridioides difficile infections. When taken orally, it is poorly absorbed.

<span class="mw-page-title-main">Whooping cough</span> Human disease caused by the bacteria Bordetella pertussis

Whooping cough, also known as pertussis or the 100-day cough, is a highly contagious, vaccine-preventable bacterial disease. Initial symptoms are usually similar to those of the common cold with a runny nose, fever, and mild cough, but these are followed by two or three months of severe coughing fits. Following a fit of coughing, a high-pitched whoop sound or gasp may occur as the person breathes in. The violent coughing may last for 10 or more weeks, hence the phrase "100-day cough". The cough may be so hard that it causes vomiting, rib fractures, and fatigue. Children less than one year old may have little or no cough and instead have periods when they cannot breathe. The incubation period is usually seven to ten days. Disease may occur in those who have been vaccinated, but symptoms are typically milder.

<i>Pseudomonas fluorescens</i> Species of bacterium

Pseudomonas fluorescens is a common Gram-negative, rod-shaped bacterium. It belongs to the Pseudomonas genus; 16S rRNA analysis as well as phylogenomic analysis has placed P. fluorescens in the P. fluorescens group within the genus, to which it lends its name.

<span class="mw-page-title-main">Pharmaceutical industry</span> Industry involved with discovery, development, production and marketing of drugs

The pharmaceutical industry is an industry involved in medicine that discovers, develops, produces, and markets pharmaceutical goods for use as drugs that function by being administered to patients using such medications with the goal of curing or preventing disease. Pharmaceutical companies may deal in "generic" medications and medical devices without the involvement of intellectual property, in "brand" materials is specifically tied to a given company's history, or in both within different contexts. The industry's has various subdivisions are all subject to a variety of laws and regulations that govern entire financial processes including the patenting, efficacy testing, safety evaluation, and marketing of these drugs. The global pharmaceuticals market produced treatments worth $1,228.45 billion in 2020, in total, and this showed a compound annual growth rate (CAGR) of 1.8% given the results of recent events.

<span class="mw-page-title-main">Eli Lilly and Company</span> American pharmaceutical company

Eli Lilly and Company, doing business as Lilly, is an American multinational pharmaceutical company headquartered in Indianapolis, Indiana, with offices in 18 countries. Its products are sold in approximately 125 countries. The company was founded in 1876 by Eli Lilly, a pharmaceutical chemist and Union Army veteran of the American Civil War for whom the company was later named.

<span class="mw-page-title-main">Natural product</span> Chemical compound or substance produced by a living organism, found in nature

A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical synthesis and have played a central role in the development of the field of organic chemistry by providing challenging synthetic targets. The term natural product has also been extended for commercial purposes to refer to cosmetics, dietary supplements, and foods produced from natural sources without added artificial ingredients.

<span class="mw-page-title-main">Protein C</span> Mammalian protein found in Homo sapiens

Protein C, also known as autoprothrombin IIA and blood coagulation factor XIV, is a zymogen, that is, an inactive enzyme. The activated form plays an important role in regulating anticoagulation, inflammation, and cell death and maintaining the permeability of blood vessel walls in humans and other animals. Activated protein C (APC) performs these operations primarily by proteolytically inactivating proteins Factor Va and Factor VIIIa. APC is classified as a serine protease since it contains a residue of serine in its active site. In humans, protein C is encoded by the PROC gene, which is found on chromosome 2.

<span class="mw-page-title-main">Fine chemical</span> Pure chemical substances produced by and for the chemical industry

In chemistry, fine chemicals are complex, single, pure chemical substances, produced in limited quantities in multipurpose plants by multistep batch chemical or biotechnological processes. They are described by exacting specifications, used for further processing within the chemical industry and sold for more than $10/kg. The class of fine chemicals is subdivided either on the basis of the added value, or the type of business transaction, namely standard or exclusive products.

<span class="mw-page-title-main">Tyrosine hydroxylase</span> Enzyme found in Homo sapiens that converts l-tyrosine to l-dopa, the precursor of cathecolamines

Tyrosine hydroxylase or tyrosine 3-monooxygenase is the enzyme responsible for catalyzing the conversion of the amino acid L-tyrosine to L-3,4-dihydroxyphenylalanine (L-DOPA). It does so using molecular oxygen (O2), as well as iron (Fe2+) and tetrahydrobiopterin as cofactors. L-DOPA is a precursor for dopamine, which, in turn, is a precursor for the important neurotransmitters norepinephrine (noradrenaline) and epinephrine (adrenaline). Tyrosine hydroxylase catalyzes the rate limiting step in this synthesis of catecholamines. In humans, tyrosine hydroxylase is encoded by the TH gene, and the enzyme is present in the central nervous system (CNS), peripheral sympathetic neurons and the adrenal medulla. Tyrosine hydroxylase, phenylalanine hydroxylase and tryptophan hydroxylase together make up the family of aromatic amino acid hydroxylases (AAAHs).

<span class="mw-page-title-main">EF-Tu</span> Prokaryotic elongation factor

EF-Tu is a prokaryotic elongation factor responsible for catalyzing the binding of an aminoacyl-tRNA (aa-tRNA) to the ribosome. It is a G-protein, and facilitates the selection and binding of an aa-tRNA to the A-site of the ribosome. As a reflection of its crucial role in translation, EF-Tu is one of the most abundant and highly conserved proteins in prokaryotes. It is found in eukaryotic mitochondria as TUFM.

<span class="mw-page-title-main">Indiana in the American Civil War</span>

Indiana, a state in the Midwest, played an important role in supporting the Union during the American Civil War. Despite anti-war activity within the state, and southern Indiana's ancestral ties to the South, Indiana was a strong supporter of the Union. Indiana contributed approximately 210,000 Union soldiers, sailors, and marines. Indiana's soldiers served in 308 military engagements during the war; the majority of them in the western theater, between the Mississippi River and the Appalachian Mountains. Indiana's war-related deaths reached 25,028. Its state government provided funds to purchase equipment, food, and supplies for troops in the field. Indiana, an agriculturally rich state containing the fifth-highest population in the Union, was critical to the North's success due to its geographical location, large population, and agricultural production. Indiana residents, also known as Hoosiers, supplied the Union with manpower for the war effort, a railroad network and access to the Ohio River and the Great Lakes, and agricultural products such as grain and livestock. The state experienced two minor raids by Confederate forces, and one major raid in 1863, which caused a brief panic in southern portions of the state and its capital city, Indianapolis.

Erskine Village is a shopping mall in South Bend, Indiana, United States. It opened in 2004 on the site of the former Scottsdale Mall, an enclosed shopping mall which featured L. S. Ayres, Ayr-Way, and Montgomery Ward. After experiencing a decline in tenancy throughout the late 1980s and into the 1990s, the property was torn down in 2003 and redeveloped the following year as a strip mall. Tenants of Erskine Village include Target, Ross Dress for Less, TJ Maxx, and Kohl's.

<span class="mw-page-title-main">Michigan Wolverines women's volleyball</span> Womans volleyball team of the University of Michigan

The Michigan Wolverines women's volleyball team represents the University of Michigan in National Collegiate Athletics Association (NCAA) Division I competition. The women's volleyball program at the University of Michigan began in 1973. Erin Virtue has been the coach since 2023. The team plays its home matches at Cliff Keen Arena.

Streptomyces isolates have yielded the majority of human, animal, and agricultural antibiotics, as well as a number of fundamental chemotherapy medicines. Streptomyces is the largest antibiotic-producing genus of Actinomycetota, producing chemotherapy, antibacterial, antifungal, antiparasitic drugs, and immunosuppressants. Streptomyces isolates are typically initiated with the aerial hyphal formation from the mycelium.

<span class="mw-page-title-main">Acyldepsipeptide antibiotics</span> Class of chemical compounds

Acyldepsipeptide or cyclic acyldepsipeptide (ADEP) is a class of potential antibiotics first isolated from bacteria and act by deregulating the ClpP protease. Natural ADEPs were originally found as products of aerobic fermentation in Streptomyces hawaiiensis, A54556A and B, and in the culture broth of Streptomyces species, enopeptin A and B. ADEPs are of great interest in drug development due to their antibiotic properties and thus are being modified in attempt to achieve greater antimicrobial activity.

<i>Streptomyces gardneri</i> Species of bacterium

Streptomyces gardneri is a bacterium species from the genus of Streptomyces. Streptomyces gardneri produces thiopeptide A, proactinomycin A, proactinomycin B, proactinomycin C.

<span class="mw-page-title-main">Vancosamine</span> Chemical compound

Vancosamines are aminosugars that are a part of vancomycin and other molecules within the vancomycin family of antibiotics. Vancosamine synthesis is encoded by the vancomycin (vps) biosynthetic cluster. Epivancosamine, a closely related aminosugar, is encoded by the chloroeremomycin (cep) biosynthetic cluster.

Chiral analysis refers to the quantification of component enantiomers of racemic drug substances or pharmaceutical compounds. Other synonyms commonly used include enantiomer analysis, enantiomeric analysis, and enantioselective analysis. Chiral analysis includes all analytical procedures focused on the characterization of the properties of chiral drugs. Chiral analysis is usually performed with chiral separation methods where the enantiomers are separated on an analytical scale and simultaneously assayed for each enantiomer.

References

  1. Debono, Manuel; Merkel, Kurt E.; Molloy, R. Michael; Barnhart, Mitchell; Presti, Eugene; Hunt, Ann H.; Hamill, Robert L. (1984). "Actaplanin, new glycopeptide antibiotics produced by Actinoplanes missouriensis. The isolation and preliminary chemical characterization of actaplanin". The Journal of Antibiotics. 37 (2): 85–95. doi: 10.7164/antibiotics.37.85 . PMID   6706856.
  2. Huber, Floyd M.; Pieper, Richard L.; Tietz, Anthony J. (January 1987). "Characterization of the process for the biosynthesis of the actaplanin complex by Actinoplanes missouriensis". Journal of Fermentation Technology. 65 (1): 85–89. doi:10.1016/0385-6380(87)90069-0.
  3. Debono, Manuel; Merkel, Kurt E.; Molloy, R. Michael; Barnhart, Mitchell; Presti, Eugene; Hunt, Ann H.; Hamill, Robert L. (1984). "Actaplanin, new glycopeptide antibiotics produced by Actinoplanes missouriensis. The isolation and preliminary chemical characterization of actaplanin". The Journal of Antibiotics. 37 (2): 85–95. doi: 10.7164/antibiotics.37.85 . PMID   6706856 . Retrieved 25 December 2014.
  4. US 4115552,Robert L Hamill&Donald C Delong,"Factor A and B of antibiotic A-4696",published 19 Sep 1978, assigned to Eli Lilly And Company
  5. US 4322406,Manuel Debono; Robert E. Weeks& Herald J. Cole,"Antibiotic A-4696 factors B1, B2, B3, C1a, C3 and E1",published 30 Mar 1982, assigned to Eli Lilly And Company
  6. Hunt, Ann H.; Elzey, Thomas K.; Merkel, Kurt E.; Debono, Manuel (February 1984). "Structures of the actaplanins". The Journal of Organic Chemistry. 49 (4): 641–645. doi:10.1021/jo00178a012.